Cuba & Mexico

Come and share the magic of Mexico and the charm of Cuba, the “colourful cousins of the Caribbean”. These two fascinating Caribbean countries will totally capture your heart.

Cuba is full of surprises and as described in the Lonely Planet, is “timeworn but magnificent, dilapidated but dignified, such fun, but at times maddeningly frustrating”. By expecting the unexpected and embracing Cuba’s eclectic culture, musicality and colour you will soon discover a country of undefinable magic.

While Mexico will captivate you with its relaxed Latin lifestyle, its bright colours and Spanish colonial architecture, catchy music and tasty cuisine, Yummy!


Our itinerary will cover Cuba's main highlights including Havana, Santiago de Cuba, Camaguey, Trinidad de Cuba, Cienfuegos, Sancti Spiritus, Santa Clara, Playa Giron on the Bay of Pigs and the beautiful Valle de Vinales. Our sightseeing excursions will involve walking, cruising the streets in classic cars and even horse carriages. Swimming, snorkelling (opt.,) and of course a Salsa dance lesson.

Havana – Old Havana was established by the Spanish in the 16th Century and today, despite 50 years of withering neglect, it is intriguingly beautiful and totally captivating.

Santiago de Cuba - Fidel Castro launched his nationalist Revolution here, Don Facundo Bacardí based his first-ever rum factory here and just about every Cuban music genre from salsa to son first emanated from here.

Camaguey – Camaguey's odd labyrinthine layout is the by-product of two centuries spent fighting off musket-toting pirates like Henry Morgan: tumultuous times led the fledgling settlement to develop a street pattern designed to confuse pillaging invaders and provide cover for its long-suffering residents.

Santa Clara - Long associated with Che Guevara, whose liberating of Santa Clara in December 1958 marked the end of the Batista regime. Visit the impressive Che Guevara monument.

Trinidad de Cuba – A World Heritage site since 1988, Trinidad is a beautifully preserved colonial town, with cobbled-stone streets and terracotta roofs. In the Valle de los Ingenios, learn about the sugar mills and slave trade that were the basis of Trinidad’s prosperity and wealth during the 18th  and  19th Centuries. Visit nearby Playa Ancon for an afternoon swim and head to the Plaza at night to enjoy the music and salsa dancing!

Cienfuegos – Established in 1819 by settlers of French origin, the city's prosperity was linked to the 19th-century sugar boom. Today, the old town remains a virtual museum of beautiful colonial buildings.

Playa Giron – Located on the Bay of Pigs, Playa Giron was one of the landing sites used by the Cuban exiles in 1961. Today it is known for its informative Museum of the Invasion and as a diving and snorkelling location.  

Valle de Vinales – The heart of Cuba’s tobacco industry, with intriguing caves and steep-sided karst mounds called mojotes.  An iconic Cuban landscape.


We will begin our Mexican journey in Guadalajara,  Mexico's second-largest city and the home of Tequila and mariachi music. From here we travel south-east staying in the illustrious silver mining city of Guanajuato, with its amazing Baroque facades and underground tunnels and in nearby San Miguel de Allende, a gorgeous little town which is often referred to as the prettiest town in Mexico.  Before reaching Mexico City, the country's most impressive Capital, we will visit the massive Teotihuacan Pyramids that date back to 300 BC.  

To conclude our time in Mexico we will move on into the vastly different world of the Yucatan Peninsula, where we will stay in colonial Merida and on the coast at Tulum on the Mayan Riviera.  The Yucatan is famous for the powder-white sand beaches of its Caribbean coast, its towering Mayan pyramids such as Chichen Itza and Uxmal and crystal clear cenotes that are just perfect for a refreshing dip on a hot day.

Guadalajara - Mexico's second largest city, the birthplace of Mariachi music and Tequila.

Guanajuato – A World Heritage Site, the old city is a living monument to its prosperous and turbulent silver mining past; for over two centuries 30% to 40% of the world's silver was mined in Guanajuato State. Delightfully colonial, Guanajuato has a maze of road tunnels beneath the town and its cobbled streets are lined by impressive buildings.  

San Miquel de Allende – A traditional town, considered by many to be the most beautiful in Mexico.

Teotihuacan - Mexico's largest ancient site where we will climb to the top of the World’s third-largest pyramid.

Mexico City - Mexico's vast capital city of 24 million people was founded by the Aztec in 1325. Today it has many wonderful museums and art galleries, and a vibrant culture.  You will be surprised !

Merida – One of Mexico's oldest cities, the Heart of the Yucatan.

Uxmal – An ancient Mayan city founded in 700AD, features a massive pyramid and impressive ceremonial buildings.

Tulum – Stay on the Riviera Maya, with white powder-sand, tepid water and palm trees literally at your doorstep, it’s the perfect spot for a relaxing beach stay. Swim in the Caribbean and the nearby freshwater cenotes, cycle (opt.) and explore Tulum’s stunningly located Mayan Ruins. 

Cancun -  An overnight stay en route back to New Zealand.


Draft Itinerary Outline  -  (subject to change)   

Day 1. Fly via Houston to Guadalajara  (Mexico)

Day 2. Guadalajara -  Visit nearby Tequila, the home of the national beverage and a fun place to visit on our first day in Mexico. Also, visit Old Town Guadalajara, which is renowned for hand-crafted silver jewellery and serenading mariachi bands.

Day 3.  Guanajuato – A morning drive will be followed by a short walking excursion to introduce you to the highlights of this historic silver town.

Day 4. San Miguel de Allende – A morning in Guanajuato before making the short drive to San Miguel in the mid-afternoon.

Day 5. San Miguel de Allende – Take part in a  fabulous  food tour

Day 6. Mexico City - Visit the impressive Teotihuacan Pyramids enroute to Mexico City.

Day 7. Mexico City - Sights will include the Palacio National to see the amazing Diego Rivera murals, the Famous Zocola the Templo Ruins and Museum and many other fascinating sights. Mexico City has so much to offer.

Day 8. Mexico City - Continue our Mexico City sightseeing.

Day 9. Merida -   Take a short afternoon flight to the Spanish Colonial City of Merida,  on the Yucatan Peninsula.

Day 10. Merida – Visit Uxmal, a most impressive Mayan site with towering pyramids that you can climb. Go swimming in a freshwater cenote before returning to the city.

Day 11. Tulum – Visit the Mayan site of Chichen itza before arriving at Tulum beach.

Day 12. Tulum  – A morning excursion to the Tulum Mayan Ruins followed by a swim in one of Tulum's most famous cenotes. In the afternoon  relax and enjoy our beautiful beach side location. Cycling is an option.

Day 13. Havana – Drive to Cancun and fly to Havana (Cuba)

Day 14. Havana – A walking tour of Old Havana and a late afternoon classic car excursion.

Day 15. Santiago de Cuba  - Sights/activities or free time in Havana until our late afternoon flight to Santiago de Cuba, the cradle of Cuba’s dance culture!

Day 16. Santiago de Cuba – A salsa lesson and an excursion to the Cemeterio de Santa Ifigenia and the 17th Century Fort of Castillo de San Pedro del Morro.

Day 17. Camaguey – After arrival, a short sightseeing walk in the Old City.

Day 18. Trinidad –  Visit impressive Sancti Spiritus before reaching the iconic colonial city of Trinidad. A late afternoon walk through the upper town at sunset and enjoy live music in the Plaza at night.

Day 19. Trinidad – A morning trip to the Valle de Ingenios,  the location of the 18th -19th Century sugar plantations and in the afternoon drive out to nearby Playa Ancon for a relaxing afternoon on the Caribbean Coast.

Day 20. Cienfuegos – Drive via Santa Clara to see the Che Guevara Museum and Monument before reaching Cienfuegos on the south coast. Ride the Malecon to our sunset dinner muster at the local Yacht Club.

Day 21. Playa Giron – Depart for the Bay of Pigs, the site of the infamous invasion in 1961. Visit the Invasion Museum and after lunch go swimming and snorkelling. Later some may wish to go cycling before dinner.

Day 22. Vinales - Drive to the far west of the island to the Valle de Vinales, the centre of Cuba’s tobacco-growing industry.

Day 23. Vinales -   A half-day tour to Indio Cave, an organic farm and a tobacco farm for a hands-on experience of how the famous Cuban Cigars are made.

Day 24. Havana – Visit  La  Finca Vigia,  Hemmingway's  Havana home before returning to our casa in Old Havana. 

Day 25. Cancun –  A free morning for last-minute shopping before our afternoon flight back to Cancun, Mexico.

Day 26. Flight to Houston  - A morning to relax, before our mid-afternoon flight to Houston and onward to Auckland.

Day 27. (dateline adjustment)



Day 28. Arrive  Auckland at around 5 or 6AM



Transport: For the most part travel by private bus/vans, taxis or classic cars. There will be two internal flights, one in Cuba and one in Mexico

Meals: In Cuba – All breakfasts included, but not lunches or dinners. Tourist restaurants are available and many casas offer excellent meals at reasonable prices.  In Mexico – all but 2 breakfasts will be included, lunches and dinners are not included. There are plenty of restaurants to choose from and markets where you can purchase supplies.

Accommodation: In Cuba we will stay in casa particulares , private homes that operate as B&B.  They are well run, clean and welcoming. Most have two rooms with private bathrooms for guests.  In Mexico we will stay in hotels.



Trip Code: CM

 Date:  Currently not scheduled

Duration: 28 days

Party: 11 to 15 + leader

Price Guide: 2019 price was $12,850 

Current Status: Keep Me Posted List